Football League Cup 2023/24, Second Round |
 | 29.08.2023 | | Portsmouth | – | Peterborough United | | 1:1 (0:1),
pen. 4:5 |
| Portsmouth |
Football League Cup 2020/21, First Round |
| 29.08.2020 | | Stevenage | – | Portsmouth | | 3:3 (3:2),
pen. 1:3 * |
| Stevenage |
Football League Cup 2010/11, Second round |
| 24.08.2010 | | Portsmouth | – | Crystal Palace | | 1:1 aet
(0:0, 1:1),
pen. 4:3 |
| Portsmouth |
Football League Cup 2000/01, Second round |
| 26.09.2000 | | Portsmouth | – | Blackburn Rovers | | 1:1 (0:0) |
| Portsmouth |
Football League Cup 2000/01, First Round |
| 22.08.2000 | | Cambridge United | – | Portsmouth | | 0:0 |
| Cambridge |
Football League Cup 1999/00, First Round |
| 17.08.1999 | | Torquay United | – | Portsmouth | | 0:0 |
| Torquay |
Football League Cup 1997/98, First Round |
| 12.08.1997 | | Peterborough United | – | Portsmouth | | 2:2 (1:2) |
| Peterborough |
Football League Cup 1996/97, Second round |
| 25.09.1996 | | Portsmouth | – | Wimbledon | | 1:1 (1:0) |
| Portsmouth |
Football League Cup 1994/95, Second round |
| 05.10.1994 | | Portsmouth | – | Everton | | 1:1 (0:1) |
| Portsmouth |
Football League Cup 1993/94, Fifth Round |
| 12.01.1994 | | Manchester United | – | Portsmouth | | 2:2 (1:1) |
| Manchester |
Football League Cup 1993/94, Fourth Round |
| 30.11.1993 | | Peterborough United | – | Portsmouth | | 0:0 |
| Peterborough |
Football League Cup 1993/94, Second round |
| 21.09.1993 | | Rotherham United | – | Portsmouth | | 0:0 |
| Rotherham |
Football League Cup 1991/92, Second round |
| 24.09.1991 | | Portsmouth | – | Oxford United | | 0:0 |
| Portsmouth |
Football League Cup 1990/91, Third round |
| 31.10.1990 | | Chelsea | – | Portsmouth | | 0:0 |
| London |
Football League Cup 1990/91, Second round |
| 25.09.1990 | | Cardiff City | – | Portsmouth | | 1:1 |
| Cardiff |
Football League Cup 1989/90, Second round |
| 03.10.1989 | | Manchester United | – | Portsmouth | | 0:0 |
| Manchester |
Football League Cup 1988/89, Second round |
| 27.09.1988 | | Portsmouth | – | Scarborough | | 2:2 |
| Portsmouth |
Football League Cup 1985/86, Fourth Round |
| 26.11.1985 | | Portsmouth | – | Tottenham Hotspur | | 0:0 * |
| Portsmouth |
Football League Cup 1985/86, Fourth Round |
| 19.11.1985 | | Tottenham Hotspur | – | Portsmouth | | 0:0 |
| London |
Football League Cup 1983/84, Second round |
| 04.10.1983 | | Portsmouth | – | Aston Villa | | 2:2 (1:0) |
| Portsmouth |
Football League Cup 1982/83, First Round |
| 14.09.1982 | | Portsmouth | – | Crystal Palace | | 1:1 |
| |
Football League Cup 1981/82, Second round |
| 27.10.1981 | | Portsmouth | – | Queens Park Rangers | | 2:2 |
| |
Football League Cup 1981/82, First Round |
| 02.09.1981 | | Southend United | – | Portsmouth | | 0:0 |
| |
Football League Cup 1980/81, Third round |
| 23.09.1980 | | Bristol Rovers | – | Portsmouth | | 0:0 |
| |
Football League Cup 1978/79, First Round |
| 12.08.1978 | | Portsmouth | – | Swindon Town | | 0:0 |
| |
Football League Cup 1977/78, Third round |
| 25.10.1977 | | Portsmouth | – | Swindon Town | | 1:1 |
| |
Football League Cup 1976/77, First Round |
| 14.08.1976 | | Crystal Palace | – | Portsmouth | | 2:2 |
| |
Football League Cup 1975/76, Second round |
| 09.09.1975 | | Portsmouth | – | Leicester City | | 1:1 |
| |
Football League Cup 1975/76, First Round |
| 20.08.1975 | | Aldershot | – | Portsmouth | | 1:1 |
| |
Football League Cup 1964/65, Second round |
| 22.09.1964 | | Watford | – | Portsmouth | | 2:2 |
| |
Football League Cup 1962/63, Fourth Round |
| 14.11.1962 | | Portsmouth | – | Sunderland | | 0:0 |
| Portsmouth |
Football League Cup 1961/62, Second round |
| 04.10.1961 | | Portsmouth | – | Derby County | | 1:1 |
| |
